Known asymmetric synthesis reaction includes asymmetric reductions, asymmetric isomerizations, asymmetric hydrosilylations and the like, and transition metal complexes with rhodium, ruthenium, iridium and the like having an optically active compound as a ligand are mainly used. Conventionally, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (hereinafter sometimes to be also abbreviated as BINAP) is generally used as an optically active phosphine. However, since the reactivity, steric selectivity, catalytic efficiency and the like of BINAP depend on the substrate and are not always sufficient, various other optically active phosphines have been produced and reported (e.g., Handbook of Enantioselective Catalysis with Transition Metal Compounds, published by VCH Verlag GmbH, 1993). Of the optically active phosphines, optically active phosphines having a dialkylamino group as a substituent are described in WO03/048174 and WO02/040491.
Of the compounds having a 1,1′-binaphthyl skeleton like BINAP, for example, JP-A-61-63690 describes that a ruthenium complex having 2,2′-bis(di(p-tolyl)phosphino)-1,1′-binaphthyl as a ligand is useful for the asymmetric reduction of a carbon-carbon double bond. JP-A-3-255090 describes that a ruthenium complex having 2,2′-bis(bis(3,5-dialkylphenyl)phosphino)-1,1′-binaphthyl as a ligand is useful for the asymmetric reduction of β-ketoester and JP-A-2004-196793 describes that a ruthenium complex having 2,2′-bis(bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino)-1,1′-binaphthyl as a ligand is useful therefor.
However, enantioselectivity or catalytic efficiency may be insufficient depending on the reaction substrate in the reactions using these transition metal catalysts.